Dyeing and printing of cellulosic textile material

ABSTRACT

A process for dyeing and printing cellulosic textile material, wherein the dye used is a compound of the general formula I ##STR1## where K is a radical of the formula ##STR2## one of the radicals X and Y is a C 2  -C 19  -carboxylic acid ester group, a C 3  -C 19  -carboxamide group, a C 4  -C 18  -sulfonamide group, a C 4  -C 8  -alkylsulfone group, a C 6  -C 8  -arylsulfone group or a sulfonic acid aryl ester group and 
     the remaining substituents X, Y and Z are hydrogen, bromine or methyl and 
     Y may also be nitro, 
     A is cyano or carbamyl, 
     B 1 , B 2  and B 3  independently of one another are aliphatic, cycloaliphatic, araliphatic or aromatic radicals, ##STR3##  is a saturated heterocyclic radical, R is hydrogen or C 1  -C 3  -alkyl, 
     one of the radicals T is a radical of the formula ##STR4##  and the other radical T is hydrogen, C 1  -C 4  -alkyl or phenyl.

The present invention relates to a process for dyeing and printing cellulosic textile material, wherein the dye used is a compound of the general formula I ##STR5## where

K is a radical of the formula ##STR6##

one of the radicals X and Y is a C₂ -C₁₉ -carboxylic acid ester group, a C₃ -C₁₉ -carboxamide group, a C₄ -C₁₈ -sulfonamide group, a C₄ -C₈ -alkylsulfone group, a C₆ -C₈ -arylsulfone group or a sulfonic acid aryl ester group,

X, Y and Z are hydrogen, bromine or methyl and

Y may also be nitro,

A is cyano or carbamyl,

B¹, B² and B³ independently of one another are aliphatic, cycloaliphatic, araliphatic or aromatic radicals. ##STR7## is a saturated heterocyclic radical,

R is hydrogen or C₁ -C₃ -alkyl,

one of the radicals T is a radical of the formula ##STR8## and

the other radical T is hydrogen, C₁ -C₄ -alkyl or phenyl.

Radicals R, other than hydrogen, are ethyl, n- or i-propyl and preferably methyl.

Examples of B¹, other than hydrogen, are the following: alkyl of 1 to 8 carbon atoms; alkyl of 2 to 8 carbon atoms which is substituted by hydroxyl, cyano, alkoxy of 1 to 8 carbon atoms, phenoxy, phenoxyethoxy or benzyloxy; cyclohexyl, norbornyl, benzyl, phenylethyl, phenylhydroxyethyl, phenylpropyl and phenylbutyl; phenyl which may or may not be substituted by chlorine, methyl, trifluoromethyl, pyrrolidonyl, methoxy or ethoxy; C₅ -C₁₂ -polyalkoxyalkyl, C₄ -C₉ -hydroxypolyalkoxyalkyl, C₁ -C₈ -alkanoyloxy-C₂ -C₆ -alkyl, C₇ -C₁₁ -aroyloxy-C₂ -C₆ -alkyl, C₁ -C₈ -alkylaminocarbonyloxy-C₂ -C₆ -alkyl, C₆ -C₁₀ -arylaminocarbonyloxy-C₂ -C₆ -alkyl and C₁ -C₈ -alkoxycarbonyl-C₂ -C₇ -alkyl; C₁ -C₁₈ -alkanoyl, C₈ -C₁₀ -aralkanoyl, C₇ -C₁₁ -aroyl, C₁ -C₄ -alkylsulfonyl and C₆ -C₁₀ -arylsulfonyl.

Specific examples of radicals B¹, in addition to those already mentioned, are:

1. Substituted or unsubstituted alkyl radicals:

CH₃, C₂ H₅, n- and i-C₃ H₇, n- and i-C₄ H₉, C₆ H₁₃, ##STR9## (CH₂)₃ O(CH₂)₄ OH, (CH₂)₂ CN, (CH₂)₅ CN, (CH₂)₆ CN, (CH₂)₇ CN, (CH₂)₂ O(CH₂)₂ CN, (CH₂)₃ O(CH₂)₂ CN, (CH₂)₂ O(CH₂)₂ O(CH₂)₂ CN, (CH₂)₃ OC₂ H₄ OCH₃, (CH₂)₃ OC₂ H₄ OC₂ H₅, (CH₂)₃ O(CH₂)₆ OH, (CH₂)₃ OC₂ H₄ OCH(CH₃)₂, (CH₂)₃ OC₂ H₄ OC₄ H₉, (CH₂)₃ OC₂ H₄ OCH₂ C₆ H₅, (CH₂)₃ OC₂ H₄ OC₂ H₄ C₆ H₅, ##STR10## CH₂ CH₂ COOH, (CH₂)₅ COOH, (CH₂)₆ COOH, the corresponding radicals in which the groups ##STR11## occur twice or three times, CH₂ CH₂ OCH₃, CH₂ CH₂ OC₂ H₅, CH₂ CH₂ OC₃ H₇, CH₂ CH₂ OC₄ H₉, CH₂ CH₂ OC₆ H₅, (CH₂)₃ OCH₃, (CH₂)₃ OC₂ H₅, (CH₂)₃ OC₃ H₇, (CH₂)₃ OC₄ H₉, ##STR12## (CH₂)₃ OC₆ H₁₃, (CH₂)₃ OC₈ H₁₇, (CH₂)₃ OCH₂ C₆ H₅, (CH₂)₃ OC₂ H₄ C₆ H₅, (CH₂)₃ OC₆ H₅, ##STR13## 2. Unsubstituted and substituted cycloalkyl and polycycloalkyl radicals: ##STR14## 3. Aralkyl radicals:

CH₂ C₆ H₅, C₂ H₄ C₆ H₅, ##STR15## and the corresponding radicals containing C₆ H₄ CH₃ instead of C₆ H₅.

4. Unsubstituted and substituted phenyl radicals:

C₆ H₅, C₆ H₄ CH₃, C₆ H₃ (CH₃)₂, C₆ H₄ OCH₃, C₆ H₄ OC₂ H₅, C₆ H₄ OCH₂ CH₂ OH and C₆ H₄ Cl;

5. The radicals:

CH₂ CH═CH₂, CH₂ COOCH₃, (CH₂)₅ COOCH₃, ##STR16## wherein n is 2, 3, 4 or 6. 6. Acyloxy radicals:

(CH₂)₂ OCHO, (CH₂)₂ OCOCH₃, (C₂ H₄ O)₂ CHO, (C₂ H₄ O)₂ COCH₃, (CH₂)₂ OCOC₃ H₇, ##STR17## (CH₂)₂ OCOC₆ H₅, (CH₂)₂ OCOC₆ H₄ CH₃, (CH₂)₂ OCOC₆ H₄ Cl, (CH₂)₂ OCOC₁₀ H₇, (CH₂)₂ OCONHCH₃, (CH₂)₂ OCONHC₄ H₉, ##STR18## (CH₂)₂ OCONHC₆ H₅, (CH₂)₂ OCONHC₆ H₄ Cl, (CH₂)₂ OCONHC₆ H₃ Cl₂, and the corresponding radicals containing (CH₂)₃, (CH₂)₄ or (CH₂)₆ instead of (CH₂)₂.

7. Acyl radicals:

CHO, CH₃ CO, C₂ H₅ CO, C₃ H₇ CO, ##STR19## C₂ H₅ CO, CH₃ C₆ H₄ CO, C₆ H₅ CH₂ CO, C₆ H₅ OCH₂ CO, CH₃ SO₂, C₂ H₅ SO₂, C₆ H₅ SO₂ and CH₃ C₆ H₄ SO₂.

Examples of preferred substituents are hydrogen, CH₃, C₂ H₅, n- and i-C₃ H₇, n- and i-C₄ H₉, C₆ H₁₃, (CH₂)₆ OH, ##STR20## (CH₂)₃ O(CH₂)₄ OH, (CH₂)₃ O(CH₂)₆ OH, CH₂ CH₂ OCH₃, CH₂ CH₂ OC₂ H₅, CH₂ CH₂ OC₄ H₉, (CH₂)₃ OCH₃, (CH₂)₃ OC₂ H₅, (CH₂)₃ OC₃ H₇, (CH₂)₃ OC₄ H₉, ##STR21## (CH₂)₃ OC₂ H₄ OCH₃, (CH₂)₃ OC₂ H₄ OC₄ H₉, (CH₂)₃ OC₂ H₄ OC₆ H₅, ##STR22## CH₂ C₆ H₅, C₂ H₄ C₆ H₅, ##STR23## C₆ H₅, C₆ H₄ CH₃, C₆ H₄ OCH₃ and C₆ H₄ OC₂ H₄ OH and (CH₂)₅ COOH.

Examples of radicals ##STR24## are pyrrolidino, piperidino, morpholino, piperazino or hexamethyleneimino.

Examples of carboxylic acid ester groups X and Y are: COOC₄ H₉ (n), COO--CH₂ --CH(CH₃)₂, COOC(CH₃)₃, COOC₄ H₈ Cl, COOC₅ H₁₁ --(n), COOCH₂ C(CH₃)₃, COOC₆ H₁₃, ##STR25## COOC₉ H₁₉, COOC₁₀ H₂₁, COOC₁₂ H₂₅, COOC₁₆ H₃₃, COOC₁₈ H₃₇, COOC₂ H₄ OC₂ H₅, COOC₂ H₄ OC₄ H₉, COOC₂ H₄ OC₆ H₅, COOCH₂ C₆ H₅, COOC₂ H₄ C₆ H₅, ##STR26## COOC₂ H₄ OC₆ H₅, COO(C₂ H₄ O)₂ CH₃, COO(C₂ H₄ O)₂ C₂ H₅, COO(C₂ H₄ O)₂ C₄ H₉, COO(C₂ H₄ O)₃ C₂ H₅ and COO(C₂ H₄ O)₃ C₄ H₉.

Examples of N-substituents of the carboxamides and sulfonamides are hydrogen, butyl, n-hexyl, phenyl, benzyl, phenylethyl, 2-phenylpropyl, 2-ethylhexyl, 1,5-dimethylhexyl, n-octyl, n-dodecyl, n-tridecyl, 6-methyl-heptyl, 3-(2-ethyl-hexoxy)-propyl, stearyl, cyclohexyl, β-methoxyethyl, β-butoxyethyl, γ-methoxypropyl, γ-butoxypropyl and γ-ethoxypropyl, as well as divalent radicals which form a pyrrolidide, piperidide or morpholide.

Examples of O-substituents of the sulfonic acid ester groups are phenyl, o-, m- and p-tolyl, o-, m- and p-chlorophenyl and 2,5-dichlorophenyl.

The dyes of the formula I may be prepared by reacting a diazo compound of an amine of the formula II ##STR27## with a coupling component of the formula KH, where K, X, Y and Z have the stated meanings.

The diazotization of the amines is carried out in a conventional manner. The coupling is also carried out in a conventional manner, in an aqueous medium, with or without addition of a solvent, at a strongly to weakly acid pH.

Preferred dyes for the process according to the invention are those which correspond to the formulae ##STR28## where B¹, B² and B³ have the stated meanings and D is a radical of the formula ##STR29## where

X¹ is a C₄ -C₁₉ -carboxylic acid ester group, a C₄ -C₁₉ -carboxamide group or a sulfonic acid phenyl ester group,

X₂ is a C₄ -C₁₉ -carboxylic acid ester group or C₄ -C₁₉ -carboxamide group and

Y¹ is a C₄ -C₁₉ -carboxylic acid ester group, a C₄ -C₁₉ -carboxamide group, a C₆ -C₁₈ -sulfonamide group or a sulfonic acid phenyl ester group which may or may not be substituted by chlorine or methyl.

Suitable processes for applying the dyes of the formula I are in particular those described in German Pat. No. 1,811,796, and German Patent Applications Nos. P 25 24 243, P 25 28 743 and P 28 55 188.4.

Details of the preparation and use of the dyes are to be found in the Examples, where parts and percentages are by weight, unless stated otherwise.

EXAMPLE 1

43.5 parts of decyl 3,5-dibromo-anthranilate are stirred in a mixture of 150 parts by volume of 100% strength acetic acid and 50 parts by volume of 100% strength propionic acid at from 0° to +5° C. 33 parts of a 42% strength nitrosylsulfuric acid are added dropwise to the mixture, and the batch is then stirred for about 30 minutes at from 0° to +5° C., until the amine has dissolved in the form of the diazonium salt. After excess nitrous acid has been removed with a small amount of aminosulfonic acid, the diazonium salt solution is run, at 0° C., into a mixture of 400 parts per volume of 85% strength acetic acid and 50 parts of sodium acetate, containing 15.5 parts of 2,6-diamino-3-cyano-4-methylpyridine in solution. After stirring the batch for several hours, whilst it gradually returns to room temperature, the dye is filtered off and washed salt-free with hot water.

A fabric of 65 parts of polyester fibers and 35 parts of mercerized cotton is impregnated with a liquor which contains 80 g/l of a 20% strength aqueous formulation of the above water-insoluble, golden yellow disperse dye of the formula ##STR30## and 80 g/l of a swelling agent and dye solvent, comprising 80 parts of a polyethylene glycol of molecular weight 1,500 and 20 parts of a reaction product of 1 mole of hexamethylenediamine and 15 moles of ethylene oxide. The pH of the liquor is brought to 6 with citric acid.

The impregnated fabric is dried for 60 seconds at 120° C. and is then heated for 60 seconds at 215° C. to fix the dye. The fabric is then rinsed cold and hot and is soaped for 20 minutes at 100° C. in the presence of a commercial detergent.

A golden yellow dyeing having good lightfastness and fastness to crocking is obtained.

EXAMPLE 2

A polyester/cotton union fabric is printed with a formulation which consists of 10 parts of the dye from Example 1, 100 parts of a reaction product of a polyethylene oxide (of molecular weight 300) with boric acid in the molar ratio of 3:1, 30 parts of oleic acid diethanolamide and 860 parts of a 3% strength alginate thickener, and the print is dried at 110° C. It is then treated for 5 minutes with live steam at 185° C., rinsed cold and soaped at 100° C. with a commercial detergent. A lightfast, washfast and solvent-fast golden yellow print on a white ground is obtained.

Using the same process on a pure cotton fabric, an equally fast print, of the same hue, is obtained.

EXAMPLE 3

32.2 parts of n-decyl 5-nitro-anthranilate are used as the diazo component, and 20.2 parts of 2,6-bis-ethylamino-3-cyano-4-methylpyridine as the coupling component under the conditions of Example 1; the dye of the formula ##STR31## is obtained.

A 65:35 polyester/cotton union fabric is printed with a paste which consists of 20 parts of this dye, 100 parts of polyethylene oxide of molecular weight 350, 30 parts of oleic acid diethanolamide and 840 parts of a 10% strength alginate thickener. The printed material is dried at 100° C. and is then fixed in 60 seconds with hot air at 190°-215° C. The print is then rinsed cold and hot and soaped at 100° C., using a commercial detergent. A bluish red print, having good lightfastness, washfastness and fastness to crocking, is obtained on a white ground.

EXAMPLE 4

Using the conditions of Example 1, but with equivalent amounts of 2-(β'-butoxyethoxy)-ethyl 5-nitroanthranilate and 2,6-bis-(β-phenyl-ethyl-amino)-3-cyano-4-methyl-pyridine, the dye of the formula ##STR32## is obtained.

A mercerized cotton twill is impregnated with an aqueous dye liquor which contains 80 g/l of the above dye and 200 g of a mixture of 80 parts of polyethylene glycol, of molecular weight 800, and 20 parts of a block polymer of 1 mole of ethylenediamine, 8 moles of propylene oxide and 8 moles of ethylene oxide. The pH of the liquor is brought to 6 with citric acid. The wet pick-up is 52%.

The fabric is then dried in a conventional manner at 120° C., and fixed for 30 seconds at 215° C. in a laboratory dryer. After rinsing and washing, a very fast, intense red dyeing is obtained, with very slight dye loss.

EXAMPLE 5

Using the conditions of Example 1, but with equivalent amounts of β-phenylethyl anthranilate and 2-(β-phenylethyl-amino)-3-cyano-4-methyl-6-amino-pyridine, the dye of the formula ##STR33## is obtained.

A fabric of 67 parts of polyester fibers and 33 parts of mercerized cotton is impregnated with a liquor which contains 100 g/l of a mixture of 80 parts of a boric acid ester of polyethylene glycol (molecular weight about 800) in the molar ratio of 1:3 and 20 parts of a reaction product of ethylenediamine with 35 moles of ethylene oxide. The wet pick-up is 80%. The fabric is dried for 15 minutes at 60°-70° C.

The treated fabric is printed with the following print paste:

    ______________________________________                                         500    parts of a 10% strength aqueous starch-ether                                   thickener                                                               2      parts of citric acid                                                    10     parts of sodium m-nitrobenzenesulfonate                                 50     parts of the above dye                                                  x      parts of water                                                          1,000  parts                                                                   ______________________________________                                    

Following fixing and afterwashing, a red print is obtained.

EXAMPLE 6

A fabric of 65 parts of polyester fibers and 35 parts of mercerized cotton is impregnated with a dye liquor which contains 20 g/l of a 20% strength formulation of the dye of the formula ##STR34## and, as a swelling agent and dye solvent, 60 g/l of a mixture of 1 part of a reaction product of 1 mole of i-octylphenol with 14 moles of ethylene oxide and 2 parts of a reaction product of 1 mole of piperazine with 16 moles of ethylene oxide. The pH of the liquor is brought to 6 with glutaric acid. The fabric is dried for only 60 seconds at 120° C. and the dye is then fixed for 30 seconds at 225° C. The fabric is rinsed cold and hot and is washed at 100° C. in the presence of a commercial detergent. A yellowish orange dyeing having good washfastness and lightfastness is obtained.

EXAMPLE 7

24 parts of 4-amino-3,5-dibromobenzoic acid (2-ethylhexyl)-amide are dissolved in 105 parts of glacial acetic acid and 15 parts by volume of concentrated hydrochloric acid are added. After cooling the mixture to 10°-15° C., 15 parts by volume of 23% strength aqueous sodium nitrite solution are run in and after stirring the mixture for 2 hours at 10°-15° C. the excess nitrous acid is destroyed in a conventional manner by adding an aqueous amidosulfonic acid solution.

The resulting solution of the diazonium salt is added gradually, at 0°-5° C., to a mixture of 14.6 g of 2,6-bis-(methoxypropylamino)-3-cyano-4-methylpyridine, 1,050 parts of glacial acetic acid, 50 parts of water and 200 parts of ice. 50 parts of sodium acetate are also added and the mixture is stirred until coupling is complete. It is then worked up by running 1,500 parts of water into the coupling solution, filtering off the precipitate, washing it with water and drying it. 31 parts of an orange powder of the formula ##STR35## are obtained.

A cotton fabric is printed, by rotary screen printing, with an ink which consists of 15 parts of the above dye, 100 parts of polyethylene oxide of molecular weight 300 and 790 parts of a 3% strength alginate thickener, and the print is dried at 100° C. It is then treated for 1 minute with hot air at 200° C., rinsed cold, soaped at the boil, again rinsed cold, and dried. A lightfast and washfast yellowish orange print on a white ground is obtained.

EXAMPLE 8

A polyester/cotton union fabric (weight ratio 50:50) is impregnated with an aqueous liquor which contains 20 g/l of a 20% strength formulation of the dye of the formula ##STR36## and, as a swelling agent and dye solvent, 50 g/l of a mixture of 80 parts of a polyethylene glycol of molecular weight 600 and 20 parts of a reaction product of 1 mole of triethanolamine with 14 moles of ethylene oxide. The pH of the liquor is brought to 7 with glutaric acid. The fabric is dried for 60 seconds at 120° C. and then heated for 90 seconds at 210° C. It is then rinsed cold and hot and washed for 5 minutes at 100° C. in the presence of a commercial detergent. A lightfast and washfast golden yellow dyeing is obtained.

EXAMPLE 9

22.12 parts of 4-amino-3,5-dibrombenzenesulfonic acid (2-ethylhexyl)-amide in 100 parts by volume of glacial acetic acid are stirred with 15 parts by volume of concentrated hydrochloric acid, and 15 parts by volume of a 23% strength aqueous sodium nitrite solution are added at 10°-15° C. The mixture is diluted with a further 62 parts by volume of glacial acetic acid and is stirred for 2 hours at 10°-15° C. After removing excess nitrous acid in a conventional manner, the diazotization mixture is added dropwise, at 0°-5° C., to a mixture of 16.95 parts of 6-amino-3-cyano-4-methyl-2-phenoxyethoxypropylaminopyridine, 1,050 parts of glacial acetic acid, 50 parts of water and 200 parts of ice. 100 parts of sodium acetate are then also added and the mixture is stirred until coupling is complete. The dye which has formed is filtered off, washed with water and dried. 28 parts of an orange powder of the formula ##STR37## are obtained.

A polyester/cotton union fabric (weight ratio 65:35) is printed with a paste which consists of 20 parts of the above dye, 120 parts of a reaction product of polyethylene oxide, of molecular weight 300, with boric acid in the molar ratio of 3:1 and 860 parts of a 10% strength alginate thickener. The print is dried at 105° C. and treated with live steam at 180° C. for 6 minutes. It is then rinsed with cold water, soaped at 80° C., rinsed cold and dried. A lightfast and washfast golden yellow print on a white ground is obtained.

    __________________________________________________________________________      ##STR38##                                                                                                                          Hue on                    Example                                                                              D                B.sub.1        B.sub.3        polyester/cotton          __________________________________________________________________________     10                                                                                    ##STR39##       H              H              golden yellow             11    "                C.sub.4 H.sub.9(n)                                                                            H              "                         12    "                                                                                                ##STR40##     H              "                         13    "                                                                                                ##STR41##     H              "                         14    "                C.sub.4 H.sub.9(n)                                                                            C.sub.4 H.sub.9(n)                                                                            "                         15                                                                                    ##STR42##       C.sub.4 H.sub.9(n)                                                                            H              "                         16    "                                                                                                ##STR43##     H              "                         17    "                C.sub.2 H.sub.4 OCH.sub.3                                                                     H              "                         18    "                C.sub.3 H.sub.6OC.sub.4 H.sub.8OH                                                             H              "                         19    "                C.sub.4 H.sub.9(n)                                                                            C.sub.4 H.sub.9(n)                                                                            "                         20    "                C.sub.3 H.sub.6 OCH.sub.3                                                                     C.sub.3 H.sub.6 OCH.sub.3                                                                     "                         21    "                C.sub.2 H.sub.4OC.sub.4 H.sub.9(n)                                                            H              "                         22    "                                                                                                ##STR44##     H              "                         23    "                "              C.sub.2 H.sub.4OC.sub.4 H.sub.9(n)                                                            "                         24    "                C.sub.3 H.sub.6OC.sub.2 H.sub.5                                                               C.sub.3 H.sub.6OC.sub.2 H.sub.5                                                               "                         25    "                C.sub.2 H.sub.5                                                                               C.sub.2 H.sub.5                                                                               "                         26    "                C.sub.2 H.sub.4OCH(CH.sub.3).sub.3                                                            C.sub.2 H.sub.4OCH(CH.sub.3).sub.3                                                            "                         27    "                                                                                                ##STR45##     C.sub.2 H.sub.4 OCH.sub.3                                                                     "                         28                                                                                    ##STR46##       H              H              "                         29    "                C.sub.4 H.sub.9                                                                               H              "                         30    "                                                                                                ##STR47##     H              "                         31    "                C.sub.3 H.sub.6OC.sub.2 H.sub.5                                                               H              "                         32    "                C.sub.2 H.sub.4OC.sub.4 H.sub.9(n)                                                            C.sub.2 H.sub.4OC.sub.4 H.sub.9(n)                                                            "                         33                                                                                    ##STR48##       H              H              "                         34    "                C.sub.2 H.sub.4OC.sub.4 H.sub.9(n)                                                            H              "                         35    "                                                                                                ##STR49##     H              "                         36                                                                                    ##STR50##       H              H              "                         37    "                C.sub.2 H.sub.4 OCH.sub.3                                                                     H              "                         38    "                C.sub.4 H.sub.9(n)                                                                            H              "                         39    "                C.sub.3 H.sub.6OC.sub.4 H.sub.8OH                                                             H              "                         40    "                C.sub.4 H.sub.9(n)                                                                            C.sub.4 H.sub.9(n)                                                                            "                         41    "                C.sub.2 H.sub.4OC.sub.4 H.sub.9(n)                                                            C.sub.2 H.sub.4OC.sub.4 H.sub.9(n)                                                            "                         42    "                C.sub.3 H.sub.6 OCH.sub.3                                                                     C.sub.3 H.sub.6 OCH.sub.3                                                                     "                         43                                                                                    ##STR51##       H              H              "                         44    "                C.sub.4 H.sub.9(n)                                                                            H              "                         45    "                                                                                                ##STR52##     H              "                         46                                                                                    ##STR53##       H              H              "                         47    "                C.sub.2 H.sub.4 OCH.sub.3                                                                     H              "                         48    "                C.sub.4 H.sub.9(n)                                                                            H              "                         49    "                  "            C.sub.4 H.sub.9(n)                                                                            "                         50    "                C.sub.2 H.sub.4OC.sub.4 H.sub.9(n)                                                            C.sub.2 H.sub.4OC.sub.4 H.sub.9(n)                                                            "                         51                                                                                    ##STR54##       H              H              "                         52    "                C.sub.4 H.sub.9(n)                                                                            H              "                         53                                                                                    ##STR55##       H              H              "                         54    "                C.sub.4 H.sub.9(n)                                                                            C.sub.4 H.sub.9(n)                                                                            "                         55    "                                                                                                ##STR56##     H              "                         56                                                                                    ##STR57##       H              H              "                         57    "                C.sub.4 H.sub.9(n)                                                                            H              "                         58    "                                                                                                ##STR58##     H              "                         59                                                                                    ##STR59##       C.sub.4 H.sub.9(n)                                                                            H              "                         60    "                                                                                                ##STR60##     H              "                         61                                                                                    ##STR61##                                                                                       ##STR62##     H              "                         62                                                                                    ##STR63##       C.sub.4 H.sub.9(n)                                                                            H              "                         63    "                                                                                                ##STR64##     H              "                         64    "                                                                                                ##STR65##     H              "                         65    "                                                                                                ##STR66##     H              "                         66    "                C.sub.3 H.sub.6OC.sub.2 H.sub.5                                                               C.sub.3 H.sub.6OC.sub.2 H.sub.5                                                               "                         67                                                                                    ##STR67##                                                                                       ##STR68##     H              "                         68                                                                                    ##STR69##       H              H              orange                    69    "                C.sub.2 H.sub.4OCH.sub.3                                                                      H              yellowish red             70    "                C.sub.2 H.sub.4OC.sub.4 H.sub.9(n)                                                            H              "                         71    "                C.sub.3 H.sub.6OCH.sub.3                                                                      H              "                         72    "                C.sub.3 H.sub.6OC.sub.2 H.sub.5                                                               H              "                         73    "                C.sub.4 H.sub.9(n)                                                                            H              "                         74    "                                                                                                ##STR70##     H              "                         75    "                                                                                                ##STR71##     H              "                         76    "                C.sub.3 H.sub.6OC.sub.4 H.sub.8OH                                                             H              "                         77    "                                                                                                ##STR72##     H              "                         78    "                                                                                                ##STR73##     H              "                         79    "                C.sub.2 H.sub.4OCH.sub.3                                                                      C.sub.2 H.sub.4OCH.sub.3                                                                      red                       80    "                C.sub.2 H.sub.4OC.sub.4 H.sub.9(n)                                                            C.sub.2 H.sub.4OC.sub.4 H.sub.9(n)                                                            "                         81    "                C.sub.3 H.sub.6OCH.sub.3                                                                      C.sub.3 H.sub.6OCH.sub.3                                                                      "                         82    "                C.sub.3 H.sub.6OC.sub.2 H.sub.5                                                               C.sub.3 H.sub.6OC.sub.2 H.sub.5                                                               "                         83    "                C.sub.4 H.sub.9(n)                                                                            C.sub.4 H.sub.9(n)                                                                            "                         84    "                                                                                                ##STR74##                                                                                     ##STR75##     "                         85    "                                                                                                ##STR76##     C.sub.3 H.sub.6OCH.sub.3                                                                      "                         86    "                                                                                                ##STR77##     C.sub.2 H.sub.4OCH.sub.3                                                                      "                         87    "                                                                                                ##STR78##                                                                                     ##STR79##     "                         88    "                                                                                                ##STR80##     C.sub.2 H.sub.4 OCH.sub.3                                                                     "                         89    "                (C.sub.2 H.sub.4OCH.sub.3).sub.2                                                              C.sub.2 H.sub.4 OCH.sub.3                                                                     "                         90    "                                                                                                ##STR81##                                                                                     ##STR82##     "                         91                                                                                    ##STR83##       H              H              orange                    92    "                C.sub.4 H.sub.9(n)                                                                            H              yellowish red             93    "                                                                                                ##STR84##     H              "                         94    "                C.sub.2 H.sub.4OC.sub.4 H.sub.9(n)                                                            H              "                         95    "                C.sub.2 H.sub.4OC.sub.4 H.sub.9(n)                                                            C.sub.2 H.sub.4OC.sub.4 H.sub.9(n)                                                            red                       96    "                C.sub.3 H.sub.6OC.sub.2 H.sub.5                                                               C.sub.3 H.sub.6OC.sub.2 H.sub.5                                                               "                         97    "                                                                                                ##STR85##                                                                                     ##STR86##     "                         98    "                C.sub.3 H.sub.6OC.sub.2 H.sub.4OCH.sub.3                                                      C.sub.3 H.sub.6OC.sub.2 H.sub.4OCH.s                                           ub.3           "                         99                                                                                    ##STR87##                                                                                       ##STR88##     H              yellowish red             100   "                                                                                                ##STR89##     H              red                       101   "                C.sub.2 H.sub.4OC.sub.4 H.sub.9(n)                                                            C.sub.2 H.sub.4OC.sub.4 H.sub.9(n)                                                            "                         102   "                C.sub.3 H.sub.6OC.sub.2 H.sub.5                                                               C.sub.3 H.sub.6OC.sub.2 H.sub.5                                                               "                         103   "                C.sub. 4 H.sub.9(n)                                                                           C.sub.4 H.sub.9(n)                                                                            "                         104   "                                                                                                ##STR90##                                                                                     ##STR91##     "                         105                                                                                   ##STR92##       C.sub.4 H.sub.9(n)                                                                            H              yellowish red             106   "                C.sub.2 H.sub.4OC.sub.4 H.sub.9(n)                                                            H              "                         107   "                                                                                                ##STR93##     H              "                         108   "                                                                                                ##STR94##     H              "                         109   "                C.sub.2 H.sub.4OC.sub.4 H.sub.9 (n)                                                           C.sub.2 H.sub.4OC.sub.4 H.sub.9                                                               red                       110   "                C.sub.3 H.sub.6 OCH.sub.3                                                                     C.sub.3 H.sub.6 OCH.sub.3                                                                     "                         111   "                C.sub.4 H.sub.9(n)                                                                            C.sub.4 H.sub.9(n)                                                                            "                         112   "                                                                                                ##STR95##                                                                                     ##STR96##     "                         113   "                                                                                                ##STR97##                                                                                     ##STR98##     "                         114   "                                                                                                ##STR99##                                                                                     ##STR100##    "                         115                                                                                   ##STR101##                                                                                      ##STR102##    H              "                         116                                                                                   ##STR103##      C.sub.3 H.sub.6 OCH.sub.3                                                                      ##STR104##    "                         117   "                  "                                                                                            ##STR105##    "                         118   "                                                                                                ##STR106##                                                                                    ##STR107##    "                         119                                                                                   ##STR108##      (CH.sub.2 ).sub.3 OCH.sub.3                                                                   (CH.sub.2).sub.3 OCH.sub.3                                                                    orange                    120   "                (CH.sub.2).sub.2 OCH.sub.3                                                                      "            "                         121                                                                                   ##STR109##        "              "            "                         122                                                                                   ##STR110##                                                                                      ##STR111##                                                                                    ##STR112##    "                         123                                                                                   ##STR113##      (CH.sub.2).sub.3 OCH.sub.3                                                                    (CH.sub.2).sub.3 OCH.sub.3                                                                    "                         124                                                                                   ##STR114##      C.sub.2 H.sub.4 OCH.sub.3                                                                     H              yellowish red             125   "                C.sub.2 H.sub.4OC.sub.4 H.sub.9(n)                                                            H              "                         126   "                C.sub.3 H.sub.6OCH.sub.3                                                                      H              "                         127   "                C.sub.3 H.sub.6OC.sub.2 H.sub.5                                                               H              "                         128   "                                                                                                ##STR115##    H              "                         129   "                                                                                                ##STR116##    H              "                         130   "                C.sub.3 H.sub.6OC.sub.4 H.sub.8OH                                                             H              "                         131   "                C.sub.2 H.sub.5                                                                               C.sub.2 H.sub.5                                                                               red                       132   "                C.sub.2 H.sub.4OCH.sub.3                                                                      C.sub.2 H.sub.4OCH.sub.3                                                                      "                         133   "                C.sub.2 H.sub.4OC.sub.4 H.sub.9(n)                                                            C.sub.2 H.sub.4OC.sub.4 H.sub.9(n)                                                            "                         134   "                C.sub.3 H.sub.6OCH.sub.3                                                                      C.sub.3 H.sub.6OC.sub.4 H.sub.8OH                                                             "                         135   "                C.sub.3 H.sub.6OCH.sub.3                                                                      C.sub.3 H.sub.6OCH.sub.3                                                                      "                         136   "                C.sub.3 H.sub.6OC.sub.2 H.sub.5                                                               C.sub.3 H.sub.6OC.sub.2 H.sub.5                                                               "                         137   "                C.sub.4 H.sub.9(n)                                                                            C.sub.4 H.sub.9(n)                                                                            "                         138   "                                                                                                ##STR117##                                                                                    ##STR118##    "                         139                                                                                   ##STR119##      C.sub.2 H.sub.4OC.sub.4 H.sub.9(n)                                                            H              yellowish red             140   "                C.sub.3 H.sub.6OC.sub.2 H.sub.5                                                               H              "                         141   "                C.sub.3 H.sub.6OC.sub.4 H.sub.8OH                                                             H              "                         142   "                C.sub.2 H.sub.4OC.sub.4 H.sub.9(n)                                                            C.sub.2 H.sub.4OC.sub.4 H.sub.9(n)                                                            red                       143   "                C.sub.3 H.sub.6OCH.sub.3                                                                      C.sub.3 H.sub.6OC.sub.4 H.sub.8OH                                                             "                         144   "                C.sub.3 H.sub.6OCH.sub.3                                                                      C.sub.3 H.sub.6OCH.sub.3                                                                      "                         145   "                C.sub.2 H.sub.4OCH.sub.3                                                                      C.sub.2 H.sub.4OCH.sub.3                                                                      "                         146   "                C.sub.3 H.sub.6OC.sub.2 H.sub.5                                                               C.sub.3 H.sub.6OC.sub.2 H.sub.5                                                               "                         147   "                C.sub.4 H.sub.9(n)                                                                            C.sub.4 H.sub.9(n)                                                                            "                         148                                                                                   ##STR120##      C.sub.2 H.sub.4OC.sub.4 H.sub.9(n)                                                            H              yellowish red             149   "                C.sub.3 H.sub.6OC.sub.2 H.sub.5                                                               H              "                         150   "                                                                                                ##STR121##    H              "                         151   "                C.sub.2 H.sub.4OC.sub.4 H.sub.9(n)                                                            C.sub.2 H.sub.4OC.sub.4 H.sub.9(n)                                                            red                       152   "                C.sub.3 H.sub.6OC.sub.2 H.sub.5                                                               C.sub.3 H.sub.6OC.sub.2 H.sub.5                                                               "                         153   "                C.sub.4 H.sub.9(n)                                                                            C.sub.4 H.sub.9(n)                                                                            "                         154   "                                                                                                ##STR122##                                                                                    ##STR123##    "                         155                                                                                   ##STR124##                                                                                      ##STR125##    H              yellowish red             156   "                C.sub.2 H.sub.4OCH.sub.3                                                                      C.sub.2 H.sub.4OCH.sub.3                                                                      red                       157   "                C.sub.3 H.sub.6OCH.sub.3                                                                      C.sub.3 H.sub.6OCH.sub.3                                                                      "                         158   "                                                                                                ##STR126##                                                                                    ##STR127##    "                         159                                                                                   ##STR128##      C.sub.3 H.sub.6 OCH.sub.3                                                                      ##STR129##    "                         160   "                C.sub.3 H.sub.6OCH.sub.3                                                                      C.sub.3 H.sub.6OCH.sub.3                                                                      "                         161   "                C.sub.2 H.sub.4OC.sub.4 H.sub.9(n)                                                            C.sub.2 H.sub.4OC.sub.4 H.sub.9(n)                                                            "                         162   "                                                                                                ##STR130##                                                                                    ##STR131##    "                         __________________________________________________________________________      ##STR132##                                                                                                                       Hue on                      Example                                                                               D                A       B.sub.1   B.sub.3  polyester/cotton            __________________________________________________________________________     163                                                                                    ##STR133##      CONH.sub.2                                                                             C.sub.4 H.sub.9(n)                                                                       H        golden yellow               164                                                                                    ##STR134##      CONH.sub.2                                                                              ##STR135##                                                                              H        "                           165                                                                                    ##STR136##      CONH.sub.2                                                                             "         H        "                           166    "                CN      C.sub.4 H.sub.9(n)                                                                       C.sub.4 H.sub.9(n)                                                                      "                           167                                                                                    ##STR137##      CONH.sub.2                                                                             C.sub.4 H.sub.9(n)                                                                       H        red                         168    "                CN      "         C.sub.4 H.sub.9(n)                                                                      red                         __________________________________________________________________________      ##STR138##                                                                                                                        Hue on                     Example                                                                               D                   R      B.sub.1  B.sub.3  polyester/cotton           __________________________________________________________________________     169                                                                                    ##STR139##                                                                                         ##STR140##                                                                           H        H        golden yellow              170                                                                                    ##STR141##         "      H        H        orange                     171                                                                                    ##STR142##         "      H                                                                                        ##STR143##                                                                             golden yellow              172                                                                                    ##STR144##         "      H        "        orange                     173                                                                                    ##STR145##         "      C.sub.2 H.sub.4OCH.sub.3                                                                 ##STR146##                                                                             orange                     174                                                                                    ##STR147##         "      "        "        red                        175                                                                                    ##STR148##         "      C.sub.3 H.sub.6OCH.sub.3                                                                "        red                        176                                                                                    ##STR149##         "      H                                                                                        ##STR150##                                                                             orange                     __________________________________________________________________________      ##STR151##                                                                                                                          Hue on                   Example                                                                              D                    R       B.sub.1B.sub.2                                                                          B.sub.3   polyester/cotton         __________________________________________________________________________     177                                                                                   ##STR152##                                                                                          ##STR153##                                                                            C.sub.4 H.sub.9(n)                                                                       ##STR154##                                                                              orange                   178                                                                                   ##STR155##          "       "        C.sub.3 H.sub.6OCH.sub.3                                                                 red                      179                                                                                   ##STR156##          CH.sub.3                                                                               C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.4OCH.sub.3                                                                 orange                   180                                                                                   ##STR157##          CH.sub.3                                                                               "        C.sub.3 H.sub.6OCH.sub.3                                                                 golden yellow            181                                                                                   ##STR158##          CH.sub.3                                                                               C.sub.4 H.sub.9(n)                                                                       ##STR159##                                                                              "                        182                                                                                   ##STR160##          CH.sub.3                                                                               "        "         red                      183                                                                                   ##STR161##          CH.sub.3                                                                               "        "         red                      __________________________________________________________________________      ##STR162##                                                                                                                       Hue on polyester,                                                              cotton                      Example                                                                             H.sub.2 ND            B.sub.1       B.sub.3   and union                   __________________________________________________________________________                                                        fabrics                     184                                                                                  ##STR163##           (CH.sub.2).sub.2 OC.sub.4 H.sub.9(n)                                                         (CH.sub.2).sub.2 OCH.sub.3                                                               yellowish orange            185  "                     C.sub.2 H.sub.4C.sub.6 H.sub.5                                                               H         golden yellow               186  "                     CH.sub.2 CH(CH.sub.3)C.sub.6 H.sub.5                                                         H         "                           187  "                     (CH.sub.2).sub.3 O(CH.sub.2).sub. 2 OC.sub.6                                   H.sub.5       H         "                           188  "                     (CH.sub.2).sub.2 OC.sub.4 H.sub.9(n)                                                         (CH.sub.2).sub.2 OC.sub.4                                                      H.sub.9n) yellowish orange            189  "                     C.sub.2 H.sub.4 C.sub.6 H.sub.5                                                              C.sub.2 H.sub.4 C.sub.6 H.sub.5                                                          "                           190  "                     (CH.sub.2).sub.2 OC.sub.4 H.sub.9(n)                                                         H         golden yellow               191  "                     (CH.sub.2).sub.3 OC.sub.2 H.sub.5                                                            (CH.sub.2).sub.3 OC.sub.2                                                      H.sub.5   yellowish orange            192  "                     C.sub.2 H.sub.4 C.sub.6 H.sub.5                                                              C.sub.2 H.sub.5                                                                          "                           193  "                     "             CH.sub.3  "                           194  "                     C.sub.4 H.sub.9(n)                                                                           C.sub.4 H.sub.9(n)                                                                       "                           195  "                     (CH.sub.2).sub.3 OCOC.sub.6 H.sub.5                                                          (CH.sub.2).sub.3 OCOC.sub.6                                                    H.sub.5   "                           196  "                     (CH.sub.2).sub.2 OCOC.sub.6 H.sub.5                                                          (CH.sub.2).sub.2 OCOC.sub.6                                                    H.sub.5   "                           197  "                     CH.sub.2 C.sub.6 H.sub.5                                                                     H         golden yellow               198  "                     (CH.sub.2).sub.3 OCH.sub.2 C.sub.6 H.sub.5                                                   H         "                           199  "                     (CH.sub.2).sub.3 O(CH.sub.2).sub.2 OC.sub.4                                    H.sub.9(n)    H         "                           200  "                     C.sub.2 H.sub.4 C.sub.6 H.sub.11                                                             H         "                           201  "                     (CH.sub.2).sub.3 OC.sub.4 H.sub.9 (n)                                                        (CH.sub.2).sub.3 OC.sub.4                                                      H.sub.9n) yellowish orange            202  "                     "             H         golden yellow               203                                                                                  ##STR164##           C.sub.2 H.sub.4C.sub.6 H.sub.5                                                               H         "                           204  "                     (CH.sub.2).sub.3 OCH.sub.3                                                                   (CH.sub.2).sub.3 OCH.sub.3                                                               yellowish orange            205  "                     (CH.sub.2).sub.3 O(CH.sub.2).sub.2 OC.sub.6                                    H.sub.5       H         golden yellow               206  "                     (CH.sub.2).sub.3 OC.sub.4 H.sub.9(n)                                                         H         golden yellow               207  "                     (CH.sub.2).sub.3 OC.sub.2 H.sub.5                                                            H         "                           208  "                     (CH.sub.2).sub.3 OC.sub.2 H.sub.5                                                            (CH.sub.2).sub.3 OC.sub.2                                                      H.sub.5   yellowish orange            209  "                     (CH.sub.2 ).sub.3 OC.sub.4 H.sub.9 (n)                                                       (CH.sub.2).sub.3 OC.sub.4                                                      H.sub.9 (n)                                                                              yellowish orange            210  "                     (CH.sub.2).sub.2 OC.sub.4 H.sub.9 (n)                                                        (CH.sub.2).sub.2 OC.sub.4                                                      H.sub.9 (n)                                                                              yellowish orange            211  "                     C.sub.4 H.sub.9(n)                                                                           H         golden yellow               212                                                                                  ##STR165##           (CH.sub.2).sub.3 OCH.sub.3                                                                   (CH.sub.2).sub.3 OCH.sub.3                                                               yellowish orange            213  "                     (CH.sub.2).sub.3 OC.sub.2 H.sub.5                                                            (CH.sub.2).sub.3 OC.sub.2                                                      H.sub.5   yellowish orange            214  "                     (CH.sub.2).sub.3 O(CH.sub.2).sub.2 OC.sub.6                                    H.sub.5       H         golden yellow               215                                                                                  ##STR166##           (CH.sub.2).sub.2 OCH.sub.3                                                                   (CH.sub.2).sub.2 OCH.sub.3                                                               golden yellow               216                                                                                  ##STR167##           (CH.sub.2).sub.3 OCH.sub.3                                                                   (CH.sub.2).sub.3 OCH.sub.3                                                               golden yellow               217  "                     C.sub.2 H.sub.4C.sub.6 H.sub.                                                                H         "                           218                                                                                  ##STR168##           (CH.sub.2).sub.3 OC.sub.2 H.sub.5                                                            (CH.sub.2).sub.3 OC.sub.2                                                      H.sub.5   yellowish orange            219  "                     (CH.sub.2).sub.3 OCH.sub.3                                                                   (CH.sub.2).sub.3 OCH.sub.3                                                               "                           220  "                     (CH.sub.2).sub.3 O(CH.sub.2).sub.2 OC.sub.6                                    H.sub.5       H         golden yellow               221  "                     (CH.sub.2).sub.2 C.sub.6 H.sub.5                                                             H         "                           222  "                     CH.sub.2 CH(CH.sub.3)C.sub.6 H.sub.5                                                         H         "                           223  "                     (CH.sub.2).sub.2 C.sub.6 H.sub.5                                                             (CH.sub.2).sub.2 C.sub.6                                                                 yellowish orange            224  "                     (CH.sub.2).sub.2 OCH.sub.3                                                                   (CH.sub.2).sub.2 OCH.sub.3                                                               "                           225  "                     (CH.sub.2).sub.2 OC.sub.4 H.sub.9 (n)                                                        (CH.sub.2).sub.2 OC.sub.4                                                      H.sub.9 (n)                                                                              "                           226                                                                                  ##STR169##           (CH.sub.2).sub.3 OCH.sub.3                                                                   (CH.sub.2).sub.3 OCH.sub.3                                                               "                           227  "                     (CH.sub.2).sub.3 OC.sub.2 H.sub.5                                                            (CH.sub.2).sub.3 OC.sub.2                                                      H.sub.5   "                           228  "                     (CH.sub.2).sub.2 OC.sub.4 H.sub.9 (n)                                                        (CH.sub.2).sub.2 OC.sub.4                                                      H.sub.9 (n)                                                                              "                           229  "                     (CH.sub.2).sub.2 OCH.sub.3                                                                   (CH.sub.2).sub.2 OCH.sub.3                                                               "                           230  "                     (CH.sub.2).sub.3 O(CH.sub.2).sub.2 OC.sub.6                                    H.sub.5       H         golden yellow               231                                                                                  ##STR170##           (CH.sub.2).sub.3 OCH.sub.3                                                                   (CH.sub.2).sub.3 OCH.sub.3                                                               yellowish orange            232  "                     C.sub.2 H.sub.4 C.sub.6 H.sub.5                                                              H         golden yellow               233                                                                                  ##STR171##           (CH.sub.2).sub.2 OCH.sub.3                                                                   (CH.sub.2).sub.2 OCH.sub.3                                                               yellowish orange            234  "                     (CH.sub.2).sub.2 C.sub.6 H.sub.5                                                             (CH.sub.2).sub.2 C.sub.6                                                                 ".sub.5                     235  "                     (CH.sub.2).sub.3 OCH.sub.3                                                                   (CH.sub.2).sub.3 OCH.sub.3                                                               "                           236  "                     C.sub.2 H.sub.4 C.sub.6 H.sub.5                                                              H         golden yellow               237  "                     (CH.sub.2).sub.2 O(C.sub.4 H.sub.9)(n)                                                       "         "                           238  "                     (CH.sub.2).sub.3 O(CH.sub.2).sub.2 OC.sub.6                                    H.sub.5       H         "                           239                                                                                  ##STR172##           (CH.sub.2).sub.2 OCH.sub.3                                                                   (CH.sub.2).sub.2 OCH.sub.3                                                               yellowish orange            240  "                     (CH.sub.2).sub.2 C.sub.6 H.sub.5                                                             (CH.sub.2).sub.2 C.sub.6                                                                 ".sub.5                     241  "                     (CH.sub.2).sub.3 OCH.sub.3                                                                   (CH.sub.2).sub.3 OCH.sub.3                                                               "                           242  "                     C.sub. 2 H.sub.4 C.sub.6 H.sub.5                                                             H         golden yellow               243  "                     (CH.sub.2).sub.3 O(CH.sub.2).sub.2 OC.sub.6                                    H.sub.5       H         "                           244                                                                                  ##STR173##           (CH.sub.2).sub.2 OCH.sub.3                                                                   (CH.sub.2).sub.2 OCH.sub.3                                                               yellowish orange            245  "                     (CH.sub.2).sub.3 OCH.sub.3                                                                   (CH.sub.2).sub.3 OCH.sub.3                                                               "                           246  "                     C.sub.2 H.sub.4 C.sub.6 H.sub.5                                                              C.sub.2 H.sub.4 C.sub.6 H.sub.5                                                          "                           247  "                     C.sub.2 H.sub.4 C.sub.6 H.sub.5                                                              H         golden yellow               248  "                     (CH.sub.2).sub.3 O(CH.sub.2).sub.2 OC.sub.6                                    H.sub.5       H         "                           249                                                                                  ##STR174##           (CH.sub.2).sub.2 OCH.sub.3                                                                   (CH.sub.2).sub.2 OCH.sub.3                                                               yellowish orange            250  "                     (CH.sub.2).sub.3 OCH.sub.3                                                                   (CH.sub.2).sub.3 OCH.sub.3                                                               "                           251  "                     C.sub.2 H.sub.4 C.sub.6 H.sub.5                                                              H         golden yellow               252  "                     (CH.sub.2).sub.3 OCH.sub.3                                                                   H         "                           253                                                                                  ##STR175##           (CH.sub.2).sub.2 OCH.sub.3                                                                   (CH.sub.2).sub.2 OCH.sub.3                                                               yellowish orange            254  "                     (CH.sub.2).sub.3 OCH.sub.3                                                                   (CH.sub.2).sub.3 OCH.sub.3                                                               "                           255  "                     C.sub.2 H.sub.4 C.sub.6 H.sub.5                                                              H         golden yellow               256  "                     (CH.sub.2).sub.2 OCH.sub.3                                                                   H         "                           257  "                     (CH.sub.2).sub.3 OCH.sub.3                                                                   H         "                           258                                                                                  ##STR176##           (CH.sub.2).sub.2 OCH.sub.3                                                                   (CH.sub.2).sub.2 OCH.sub.3                                                               yellowish orange            259  "                     (CH.sub.2).sub.3 OCH.sub.3                                                                   (CH.sub.2).sub.3 OCH.sub.3                                                               "                           260  "                     (CH.sub.2).sub.3 OCH.sub.3                                                                   H         golden yellow               261                                                                                  ##STR177##           (CH.sub.2).sub.2 OCH.sub.3                                                                   (CH.sub.2).sub.2 OCH.sub.3                                                               yellowish orange            262  "                     (CH.sub.2).sub.3 OCH.sub.3                                                                   (CH.sub.2).sub.3 OCH.sub.3                                                               "                           263  "                     (CH.sub.2).sub.3 OCH.sub.3                                                                   H         golden yellow               264  "                     C.sub.2 H.sub.4 C.sub.6 H.sub.5                                                              H         "                           265                                                                                  ##STR178##           (CH.sub.2).sub.3 OCH.sub.3                                                                   (CH.sub.2).sub.3 OCH.sub.3                                                               yellowish orange            266  "                     (CH.sub.2).sub.2 OCH.sub.3                                                                   (CH.sub.2).sub.2 OCH.sub.3                                                               "                           267                                                                                  ##STR179##           C.sub.2 H.sub.4 C.sub.6 H.sub.                                                               C.sub.2 H.sub. 4 C.sub.6                                                                 ".sub.5                     268  "                     "             H         golden yellow               269                                                                                  ##STR180##           (CH.sub.2).sub.2 OCH.sub.3                                                                   (CH.sub.2).sub.2 OCH.sub.3                                                               yellowish orange            270                                                                                  ##STR181##           C.sub.2 H.sub.4 C.sub.6 H.sub.5                                                              H         golden yellow               271  "                     (CH.sub.2).sub.2 OCH.sub.3                                                                   H         "                           272                                                                                  ##STR182##           (CH.sub.2).sub.2 OCH.sub.3                                                                   H         "                           273  "                     (CH.sub.2).sub.3 OCH.sub.3                                                                   H         "                           274                                                                                  ##STR183##           C.sub.2 H.sub.4 C.sub.6 H.sub.5                                                              C.sub.2 H.sub.4 C.sub.6 H.sub.5                                                          yellowish orange            275  "                     "             H         golden yellow               276                                                                                  ##STR184##           C.sub.2 H.sub.4 C.sub.6 H.sub.5                                                              C.sub.2 H.sub.4 C.sub.6 H.sub.5                                                          yellowish orange            277  "                     "             H         golden yellow               278                                                                                  ##STR185##           (CH.sub.2).sub.3 OCH.sub.3                                                                   (CH.sub.2).sub.3 OCH.sub.3                                                               red                         279  "                     (CH.sub.2).sub.2 OC.sub.4 H.sub.9 (n)                                                        (CH.sub.2).sub.2 OC.sub.4                                                      H.sub.9 (n)                                                                              "                           280                                                                                  ##STR186##           (CH.sub.2).sub.3 OCH.sub.3                                                                   (CH.sub.2).sub.3 OCH.sub.3                                                               "                           281  "                     (CH.sub.2).sub.2 OC.sub.4 H.sub.9 (n)                                                        (CH.sub.2).sub.2 OC.sub.4                                                      H.sub.9 (n)                                                                              "                           282  "                     C.sub.2 H.sub.4 C.sub.6 H.sub.5                                                              H         "                           283                                                                                  ##STR187##           C.sub.2 H.sub.4 OC.sub.4 H.sub.9 (n)                                                         C.sub.2 H.sub.4 C.sub.6 H.sub.5                                                          golden yellow               284  "                     C.sub.2 H.sub.4 C.sub.6 H.sub.5                                                              H         "                           285  "                     C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OC.sub.6                                      H.sub.5       H         "                           286  "                     "             C.sub.3 H.sub.6 OC.sub.2 H.sub.4                                               OC.sub.6 H.sub.5                                                                         "                           287  "                     C.sub.2 H.sub.4 C.sub.6 H.sub.11                                                             C.sub.2 H.sub.4 C.sub.6 H.sub.11                                                         "                           288                                                                                  ##STR188##           (CH.sub.2).sub.3 OCH.sub.3                                                                   (CH.sub.2).sub.3 OCH.sub.3                                                               orange                      289  "                     (CH.sub.2).sub.3 OC.sub.4 H.sub.9 (n)                                                        (CH.sub.2).sub.3 OC.sub.4                                                      H.sub.9 (n)                                                                              "                           290  "                                                                                                     ##STR189##   H         "                           291  "                     (CH.sub.2).sub.2 OC.sub.4 H.sub.9 (n)                                                        H         "                           292                                                                                  ##STR190##           (CH.sub.2).sub.3 O(CH.sub.2).sub.2 OC.sub.6                                    H.sub.5       H         golden yellow               293  "                     (CH.sub.2).sub.2 C.sub.6 H.sub.5                                                             H         "                           294                                                                                  ##STR191##           (CH.sub.2).sub.3 O(CH.sub.2).sub.2 OC.sub.6                                    H.sub.5       H         "                           295                                                                                  ##STR192##           (CH.sub.2).sub.3 O(CH.sub.2).sub.2 OC.sub.6                                    H.sub.5       H         "                           296                                                                                  ##STR193##           C.sub.2 H.sub.4 C.sub.6 H.sub.5                                                              H         yellowish red               297  "                     "             C.sub.2 H.sub.4                                                                          redub.6 H.sub.5             298                                                                                  ##STR194##           C.sub.2 H.sub.4 C.sub.6 H.sub.5                                                              H         golden yellow               299  "                     (CH.sub.2).sub.3 O(CH.sub.2).sub.2 OC.sub. 6                                   H.sub.5       H         "                           300                                                                                  ##STR195##           (CH.sub.2).sub.3 O(CH.sub.2).sub.2 OC.sub.6                                    H.sub.5       H         "                           301  "                     C.sub.2 H.sub.4 C.sub.6 H.sub.5                                                              H         "                           302                                                                                  ##STR196##           C.sub.2 H.sub.4 C.sub.6 H.sub.5                                                              H         yellowish red               303  "                     "             C.sub.2 H.sub.4 C.sub.6 H.sub.5                                                          red                         304                                                                                  ##STR197##           (CH.sub.2 ).sub.3 O(CH.sub.2).sub.2 OC.sub.6                                   H.sub.5       H         golden                      __________________________________________________________________________                                                        yellow                       ##STR198##                                                                    Example H.sub.2 ND            B.sub.1B.sub.2                                                                         B.sub.3       Hue                        __________________________________________________________________________     305                                                                                     ##STR199##           C.sub.4 H.sub.9n                                                                       C.sub.6 H.sub.5                                                                              golden yellow              306     "                     "       C.sub.3 H.sub.6 OCH.sub.3                                                                    "                          307     "                     CH.sub.3                                                                               C.sub.2 H.sub.4 OC.sub.4 H.sub.9n                                                            "                          308                                                                                     ##STR200##           C.sub.4 H.sub.9n                                                                       C.sub.3 H.sub.6 OCH.sub.3                                                                    yellowish red              309     "                     "       C.sub.3 H.sub.6 OCH.sub.2C.sub.6                                               H.sub.5       "                          310                                                                                     ##STR201##           CH.sub.3                                                                               C.sub.2 H.sub.4 C.sub.6 H.sub.5                                                              golden yellow              311     "                     C.sub.4 H.sub.9n                                                                       C.sub.2 H.sub.4 C.sub.6 H.sub.5                                                              "                          312     "                     "       C.sub.3 H.sub.6 OCH.sub.3                                                                    "                          313                                                                                     ##STR202##           "       C.sub.2 H.sub.4 C.sub.6 H.sub.5                                                              "                          314                                                                                     ##STR203##           "       C.sub.3 H.sub.6 OCH.sub.3                                                                    "                          315     "                     "       C.sub.2 H.sub.4 C.sub.6 H.sub.5                                                              "                          316     "                     "       CH.sub.2 C.sub.6 H.sub.5                                                                     "                          __________________________________________________________________________      ##STR204##                                                                    Example  D                    B.sup.1       B.sup.3    Hue                     __________________________________________________________________________     317                                                                                      ##STR205##          (CH.sub.2).sub.3 OCH.sub.3                                                                   CH(CH.sub.3).sub.2                                                                        red                     318                                                                                      ##STR206##          "             "          "                       319                                                                                      ##STR207##          "             "          "                       320                                                                                      ##STR208##          "             "          "                       321                                                                                      ##STR209##          "             "          "                       322                                                                                      ##STR210##          CH(CH.sub.3).sub.2                                                                           "          "                       323                                                                                      ##STR211##          "             "          "                       324                                                                                      ##STR212##          "             "          "                       325                                                                                      ##STR213##                                                                                          ##STR214##   "          "                       326                                                                                      ##STR215##          "             "          "                       327                                                                                      ##STR216##          "             "          "                       328                                                                                      ##STR217##          "             "          "                       329                                                                                      ##STR218##          "             "          "                       330                                                                                      ##STR219##                                                                                          ##STR220##   "          "                       331                                                                                      ##STR221##          "             "          "                       332                                                                                      ##STR222##                                                                                          ##STR223##                                                                                   ##STR224##                                                                               "                       333      "                                                                                                    ##STR225##   CH(CH.sub.3).sub.2                                                                        "                       334      "                    "                                                                                             ##STR226##                                                                               "                       __________________________________________________________________________ 

We claim:
 1. A process for dyeing and printing cellulosic textile material, comprising contacting said cellulosic textile material with a swelling agent and a dye wherein the dye used is a compound of the general formula I ##STR227## where K is a radical of the formula ##STR228## one of the radicals X and Y is a C₂ -C₁₉ -carboxylic acid ester group, a C₃ -C₁₉ -carboxamide group, a C₄ -C₁₈ -sulfonamide group, a C₄ -C₈ -alkylsulfone group, a C₆ -C₈ -arylsulfone group or a sulfonic acid aryl ester group andthe remaining substituents X, Y and Z are hydrogen, bromine or methyl and Y may also be nitro, A is cyano or carbamyl, B¹, B² and B³ independently of one another are aliphatic, cycloaliphatic, araliphatic or aromatic radicals, ##STR229## is a saturated heterocyclic radical, R is hydrogen or C₁ -C₃ -alkyl, one of the radicals T is a radical of the formula ##STR230## and the other radical T is hydrogen, C₁ -C₄ -alkyl or phenyl.
 2. A process as claimed in claim 1, wherein the dye used is a compound of the general formula ##STR231## where K is a radical of the formula ##STR232## one of the radicals X and Y is a C₂ -C₁₉ -carboxylic acid ester group or a C₃ -C₁₉ -carboxamide group and the two remaining radicals X and Z or Y and Z are bromine, or X is a C₂ -C₁₉ -carboxylic acid ester group or a C₃ -C₁₉ -carboxamide group, Y is nitro and Z is hydrogen,B¹ is hydrogen, C₁ -C₈ -alkyl, allyl, C₁ -C₃ -alkyl which is substituted by C₁ -C₄ -alkoxy, phenoxy, phenoxyethoxy or phenyl, C₅ -C₁₂ -polyalkoxyalkyl, cyclohexyl or unsubstituted or substituted phenyl, B² is hydrogen or is defined like B¹ or B¹ and B² together with the nitrogen form a saturated 5-membered to 7-membered ring.
 3. A process as claimed in claim 1, wherein the dye used is a compound of the formula ##STR233## where B¹, B² and B³ have the stated meanings andD is a radical of the formula ##STR234## where X¹ is a C₄ -C₁₉ -carboxylic acid ester group, a C₄ -C₁₉ -carboxamide group or a sulfonic acid phenyl ester group,X² is a C₄ -C₁₉ -carboxylic acid ester group or a C₄ -C₁₉ -carboxamide group and Y¹ is a C₄ -C₁₉ -carboxylic acid ester group, a C₄ -C₁₉ -carboxamide group, a C₆ -C₁₈ -sulfonamide group or a sulfonic acid phenyl ester group which is unsubstituted or substituted by chlorine or methyl. 